Hydrochloric Acid → 7-Iodo-5-methoxyimidazo[1,2-a]pyridine

Temperature

80 °C

To a mixture of bromoacetaldehyde dimethylacetal (4.50 ml, 37.1 mmol) in water (126 ml) was added a 1M solution of hydrochloric acid (8.40 ml, 8.40 mmol). After 2.5 h the reaction mixture was heated to 80° C. resulting in a clear solution. After 40 minutes the reaction mixture was cooled to ambient temperature and sodium bicarbonate (3.83 g, 45.6 mmol) and 4-iodo-6-methoxypyridin-2-amine (5.25 g, 21.0 mmol) were added. After 16 hours the reaction mixture was diluted with ethyl acetate, washed with water, then dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (methanol/dichloromethane gradient) to give 7-iodo-5-methoxyimidazo[1,2-a]pyridine. LRMS (ESI) calculated for C8H8IN2O [M+H]+, 275.0 found 274.9.

1. customresulting in a clear solution
2. temperatureAfter 40 minutes the reaction mixture was cooled to ambient temperature
3. washwashed with water
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by column chromatography on silica gel (methanol/dichloromethane gradient)

ORD record

ord-369cb5a8b09e495ea775380a7c6dfb85

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455477B2